A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Winchester bed & breakfast

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

1. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (99 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
$399 nightly
The price is $460
Oct 1 - Oct 2
Total with taxes and fees
Glen Gordon Manor
A spacious living room with a wooden floor, a large sofa, a coffee table, and a dining area with a wooden table and chairs.

2. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (332 reviews)
"Great location and service. A perfect weekend getaway from DC or Richmond."
United States
Mindi
$150 nightly
The price is $171
Sep 27 - Sep 28
Total with taxes and fees
Loudoun Valley Manor
A two-story house with a front porch, American flags, and a mailbox.

3. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (456 reviews)
"Amazing place with incredible history!"
United States
Andrea
$155 nightly
The price is $176
Oct 5 - Oct 6
Total with taxes and fees
The Carriage Inn B&B
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.

4. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (146 reviews)
"This is a very nice and relaxing inn with very helpful staff"
United States
David
$165 nightly
The price is $177
Oct 6 - Oct 7
Total with taxes and fees
Light Horse Inn
A hallway with a dark wooden floor, white walls, and a large mirror on the right. There is a door at the end of the hallway and a small table with a vase of flowers on the left.

5. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (140 reviews)
"A very beautiful experience. The staff was amazing. The country club access was such a treat. The room was breathtaking. We can’t wait to go back:"
United States
Adriane
$238 nightly
The price is $271
Sep 24 - Sep 25
Total with taxes and fees
Inn at Evergreen
A two-story house with a porch and a small garden area.

6. Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (38 reviews)
"Staff was wonderful and caring! Breakfast was delicious. The tavern had wonderful beer and we enjoyed meeting Norman the beagle."
United States
Deborah
$320 nightly
The price is $369
Sep 27 - Sep 28
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
A cozy seating area with two rocking chairs and a small table, overlooking a lush garden through a large arched window.

7. Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (36 reviews)
"Super cute place! Drew was so helpful and friendly. Loved the breakfast and the whole vibe of the house. Highly recommend,"
United States
Kathryn
$359 nightly
The price is $387
Sep 24 - Sep 25
Total with taxes and fees
Gay Street Inn
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

8. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
$648 nightly
The price is $739
Sep 23 - Sep 24
Total with taxes and fees
The Inn at Grass Roots Hill
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

9. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
$161 nightly
The price is $177
Oct 6 - Oct 7
Total with taxes and fees
Hillbrook Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"Clean room and quiet"
Stephanie 1-night trip
Posted 12 hours ago
Spark by Hilton Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
788
Accommodation
47 B&B
Lowest Price
$171
Highest Price
$739

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $171 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant fall months of September and October. This period attracts travelers looking to experience the stunning autumn foliage and partake in various local events, all while enjoying the comfortable temperatures ranging from the mid-50s to low 70s Fahrenheit. The scenery is particularly enchanting as the leaves change, creating a picturesque backdrop for outdoor activities such as hiking the nearby trails or exploring the charming downtown area.

September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter.
What is the difference between a Winchester Bed & Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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